On The Cover: Keith Carollo

Growing up in suburban Illinois, Keith Carollo remembers driving with his family into Chicago and passing the billboard for the Magikist Carpet Cleaning company on their way into the city. The Magikist logo? A giant pair of red lips. Lips figure prominently in Carollo's work, partly because of this childhood resonance—lips act as symbols of culture and urbanity—but also because of their graphic simplicity. "I can't really draw a face," says Carollo, "but lips are easy."

Easy or not, a couple of pairs of Carollo's lips popped up on the sides of buildings in Kingston for the O+ Festival, part of the event's mural program. The floating red appendages surprise the viewer in their industrial context, at once sensual, goofy, and sophisticated, reminiscent in equal parts of Milton Glaser and Francis Cugat's book cover for The Great Gatsby. "I hope there's some little kid who will love them and be inspired by them like I was," he says. Carollo also has a fascination with swans, whose silhouettes often appear in his work. "I guess I'm like a big girl," Carollo says, and laughs. "I like lips and swans."

Back in 1998, Carollo and his husband Chris Bick started e-tailer Fredflare.com, selling Urban Outfitters-style novelty gift items, clothing, and accessories. Growing the company from a start-up in their apartment to a 20-person Internet dynamo took a toll on the pair, and they sold the company earlier this year and relocated to their weekend house in Mount Tremper. This has allowed them to focus on creative adventures—for Carollo, art ("I always dreamed of going to art school," he says); for Bick, pursuing an acting career. Bick will be starring in the STS Playhouse production of "The Lady in Question" this month. Bick is in character as the femme fatale Gertrude Garnett in the cover image.

Carollo credits his stepfather, a clown by profession, for instilling in him the freedom to follow his intuition and not worry about having a traditional job. (He notes that his stepfather went bankrupt.)

Simplicity is a guiding principle for Carollo, who has a background in graphic design. "I've always loved to play with colors, shapes, geometry," he says. "I like getting to the essence of things." On his Etsy page, there is currently one item for sale (Carollo hopes to have more pieces up for the holiday season), a laser-cut melamine phrase: Don't Worry About It. Eleven inches square and a quarter-inch thick, it can be used as either wall art or a trivet. This marriage of inspirational phrases, art, and practicality is classic Carollo. "The things I make are somewhere between Ellsworth Kelly and a fuzzy kitty 'Hang in There!' poster," he says.